When listening to music- your favorites- try to spend an hour at least, at levels you enjoy, maybe a bit louder. If after an hour or 2
1. you want more and you are reluctant to end- good sign.
2. relieved to turn things off and leave the room- bad sign.
#1. For me usually involves tubes, either in the amps or preamp. Tubes seem to allow for longer, more enjoyable listening sessions.
#2 SS amps tend to be fatuiging after long sessions, especially at higher volumes. SS also seems flat and uninvlolving.
My advice (see Kurt:).
Unlike other advice offered, I think amps and pre are first. In my experience, I find that most speakers I put in my system sound very good, from monitors to floorstanders and I could live with many which have passed through my room. But, I would be extremely reluctant to let go of my amps and pre now that I have a wonderful match and I have heard beautiful MUSIC from many different speakers. Then it's just a matter of tuned bass and room acoustics (yes, I know, the right speakers! But, many speakers are acceptable).
As a matter of fact, I regret having sold a pair or 2.
But that's how this hobby is, you live and learn.
My advice- listen for an extended period of time- if your head hurts and your ears need a break- BAD!
If just want to keep groovin' on the music for hours and hours, turning it up- GOOD!